3-氯-丙烷-1-磺酸丁酯 | 146475-47-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 中文名称: 3-氯-丙烷-1-磺酸丁酯
• 中文别名: 3-氯丙磺酸丁酯
• 英文名称: 1-butyl 3-chloro-1-propanesulfonate
• 英文别名: butyl 3-chloro-1-propanesulfonate；n-butyl 3-chloro-1-propanesulfonate；Butyl 3-chloropropylsulfonate；butyl 3-chloropropane-1-sulfonate
• CAS: 146475-47-0
• 化学式: C₇H₁₅ClO₃S
• 分子量: 214.713
• InChiKey: MJHBOVFGBJXYQE-UHFFFAOYSA-N

物化性质

• 沸点：
  328.4±25.0 °C(Predicted)
• 密度：
  1.174±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿、二氯甲烷、乙酸乙酯、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-氯-丙烷-1-磺酸丁酯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以90%的产率得到环丙烷磺酸丁酯
  参考文献：
  名称：

  Organic sulfur mechanisms. 36. Cyclopropanesulfonyl chloride: its mechanisms of hydrolysis and reactions with tertiary amines in organic media

  摘要：

  Cyclopropanesulfonyl chloride (1) has been synthesized and its reactions examined to see if the three-membered ring leads to unusual reactions in either 1 or the corresponding sulfene, cyclopropanethione S,S-dioxide (2). pH-rate profiles, primary kinetic isotope effects (KIE's), and pH-product ratio experiments are in full agreement with mechanisms of hydrolysis of 1 like those of a simple alkanesulfonyl chlorides (J. Am. Chem. Soc. 1992,114,1743-1749), specifically, (a) below pH 7.2 by S(N)2-S reaction with water and (b) above pH 7.3, elimination by hydroxide to form the sulfene (2) which is trapped by (i) water below pH 12.0 and (ii) hydroxide above pH 12.0. The products of the reaction of cyclopropanesulfonyl-1-d chloride (9) with triethylamine and 2-propanol in dichloromethane indicate that most of the reaction goes via 2; the analogous reaction with trimethylamine apparently proceeds by a direct formation of the sulfonylammonium chloride (14) which then yields the alpha-deuterated N,N-dimethyl sulfonamide (12, R = Me). The evident sulfene formation processes in the reaction of triethylamine with ethanesulfonyl, 2-propanesulfonyl, and cyclopropanesulfonyl chlorides show very low primary KIE's (<1.5), pointing to highly product-like transition states. Reaction of 1 with an enamine (1-pyrrolidino-2-methylpropene, 20) in the presence of a base in either water or dichloromethane gave cyclopropanesulfonpyrrolidide (23) and an aldehyde adduct (24), but no four-membered cycloadduct (21).

  DOI：

  10.1021/jo00057a027
• 作为产物：
  描述：

  3-氯丙烷磺酰氯 、 正丁醇 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以76%的产率得到3-氯-丙烷-1-磺酸丁酯
  参考文献：
  名称：

  Organic sulfur mechanisms. 36. Cyclopropanesulfonyl chloride: its mechanisms of hydrolysis and reactions with tertiary amines in organic media

  摘要：

  Cyclopropanesulfonyl chloride (1) has been synthesized and its reactions examined to see if the three-membered ring leads to unusual reactions in either 1 or the corresponding sulfene, cyclopropanethione S,S-dioxide (2). pH-rate profiles, primary kinetic isotope effects (KIE's), and pH-product ratio experiments are in full agreement with mechanisms of hydrolysis of 1 like those of a simple alkanesulfonyl chlorides (J. Am. Chem. Soc. 1992,114,1743-1749), specifically, (a) below pH 7.2 by S(N)2-S reaction with water and (b) above pH 7.3, elimination by hydroxide to form the sulfene (2) which is trapped by (i) water below pH 12.0 and (ii) hydroxide above pH 12.0. The products of the reaction of cyclopropanesulfonyl-1-d chloride (9) with triethylamine and 2-propanol in dichloromethane indicate that most of the reaction goes via 2; the analogous reaction with trimethylamine apparently proceeds by a direct formation of the sulfonylammonium chloride (14) which then yields the alpha-deuterated N,N-dimethyl sulfonamide (12, R = Me). The evident sulfene formation processes in the reaction of triethylamine with ethanesulfonyl, 2-propanesulfonyl, and cyclopropanesulfonyl chlorides show very low primary KIE's (<1.5), pointing to highly product-like transition states. Reaction of 1 with an enamine (1-pyrrolidino-2-methylpropene, 20) in the presence of a base in either water or dichloromethane gave cyclopropanesulfonpyrrolidide (23) and an aldehyde adduct (24), but no four-membered cycloadduct (21).

  DOI：

  10.1021/jo00057a027

文献信息

• INHIBITION OF MEMAPSIN 1 CLEAVAGE IN THE TREATMENT OF DIABETES
  申请人：Tang Jordan

  公开号：US20130261052A1

  公开（公告）日：2013-10-03

  Proteases such as memapsin-1 are import enzymes, playing roles in a variety of diseases including diabetes. The inventors have developed inhibitors of memapsin 1 and methods of use therefore in the treatment of disease.

  蛋白酶如膜蛋白酶-1是重要的酶，发挥着在包括糖尿病在内的多种疾病中的作用。发明者们已经开发出膜蛋白酶1的抑制剂以及在治疗疾病中的使用方法。
• Inhibitors of Memapsin 2 Cleavage for the Treatment of Alzheimer's Disease
  申请人：Purdue Research Foundation

  公开号：US20140066488A1

  公开（公告）日：2014-03-06

  Proteases such as memapsin 2 are important enzymes, playing roles in a variety of diseases including Alzheimer's Disease. The inventors have developed inhibitors of memapsin 2 and methods of use therefore in the treatment of disease.

  蛋白酶如膜蛋白酶2是重要的酶，发挥着在各种疾病中的作用，包括阿尔茨海默病。发明者已经开发了膜蛋白酶2的抑制剂以及在治疗疾病中使用的方法。
• DERIVATIVES OF N-(ARYLAMINO) SULFONAMIDES AS INHIBITORS OF MEK
  申请人：Maderna Andreas

  公开号：US20080058340A1

  公开（公告）日：2008-03-06

  This invention concerns N-(2-arylamino) aryl sulfonamides, which are inhibitors of MEK and are useful in treatment of cancer and other hyperproliferative diseases.

  这项发明涉及N-(2-芳基氨基)芳基磺酰胺，它们是MEK的抑制剂，可用于治疗癌症和其他过度增殖性疾病。
• DERIVATIVES OF N-(ARYLAMINO) SULFONAMIDES INCLUDING POLYMORPHS AS INHIBITORS OF MEK AS WELL AS COMPOSITIONS, METHODS OF USE AND METHODS FOR PREPARING THE SAME
  申请人：Vernier Jean-Michel

  公开号：US20110060049A1

  公开（公告）日：2011-03-10

  This invention concerns N-(2-arylamino) aryl sulfonamide compounds which are inhibitors of MEK including crystalline polymorphic forms which exhibit a specific powder x-ray diffraction profile and/or a specific differential scanning calorimetry profile. This invention also concerns pharmaceutical compositions comprising the compounds described herein and methods of use of the compounds and compositions described herein, including the use in the treatment and/or prevention of cancer, hyperproliferative diseases and inflammatory conditions. The invention also concerns methods of making the compounds and compositions described herein.

  本发明涉及N-(2-芳基氨基)芳基磺酰胺化合物，其是MEK抑制剂，包括具有特定粉末X射线衍射谱和/或特定差示扫描量热谱的晶体多态形式。本发明还涉及包含所述化合物的制药组合物及所述化合物和组合物的使用方法，包括在治疗和/或预防癌症、高增殖性疾病和炎症疾病中的使用。本发明还涉及制备所述化合物和组合物的方法。
• Derivatives of N-(arylamino) sulfonamides as inhibitors of MEK
  申请人：Ardea Biosciences

  公开号：US07759518B2

  公开（公告）日：2010-07-20

  This invention concerns N-(2-arylamino)aryl sulfonamides, which are inhibitors of MEK and are useful in treatment of cancer and other hyperproliferative diseases.

  这项发明涉及N-(2-芳基氨基)芳基磺酰胺，它们是MEK的抑制剂，并且在治疗癌症和其他过度增殖性疾病方面非常有用。